The school is separated into two distinct campuses; the Lower School campus houses kindergarten through sixth grade students, while the Upper School houses seventh through twelfth grade students. The two campuses are distinct yet interrelated, and school functions take place regularly at both locations. The two campuses are located less than two miles from one another.

Two wings of the school exist side by side: K-2 and 3-6. Each encompasses its own facilities for individual and collaborative study. The oval Beit Midrash located at the entrance is regularly used for tefilah. Other notable facilities include the Great Books Reading Room, "Field of Dreams" Playground, technology labs, science classrooms, and a library with two designated working classrooms.

Since 1976, the Lower School has undergone three major renovations. The school now occupies approximately 130,000 square feet (12,000 m2) on 11 acres (45,000 m2) and houses over 700 Lower School students.

The central hallway, the "Cardo", is bracketed by arches modeled on the archways in the ancient Jewish Quarter of ByzantineJerusalem. The main thoroughfare showcases student art and other projects.

Throughout the structure are pieces of Jewish history and acknowledgments of the foundation of pluralism on which the school was established. The Beit Midrash features rounded stained glass windows circling a cupola based on Eastern European synagogue design, with each panel representing an essential principle of Judaism, including Torah, Neshamah (Soul), Kavanah (Spirit), Tikkun Olam (Repairing the World) and Rachamim (Compassion). A woodworking motif frames the room and Jerusalem stone is featured throughout. The doorposts in the school have distinct mezuzot.

Spaces for the arts and athletics include the Daniel Pearl Memorial Gym which holds 700 and encompasses full-court basketball play. Art spaces include a ceramics studio with six pottery wheels and state-of-the-art kiln, a professionally equipped photography studio, dark room, and a recording studio.

Lower School students spend 60% of their day on General Studies and 40% on Judaic studies. Each day is labeled with a letter from A to F. Each "Letter" day has a different schedule. After the Lower School finishes with F, they restart the cycle. In addition to a core curriculum, the academic calendar is dotted with holiday celebrations, visiting artists days, and field trips.

Lower School students are introduced to Judaics and Hebrew through a combination of classroom instruction and experiences. The study of Hebrew begins with Tal Am, a curriculum based on creating a visual and oral environment for learning. By the end of their first grade, children are comfortable reading out of the siddur (prayer book). In the third grade, students begin to study Ivrit b'Ivrit, in which every class in Judaics is taught in Hebrew.

Inspiring a spiritual connection to Judaism is central in the elementary grades. A sense of celebration surrounds tefilah. Children are encouraged to explore their ideas about God by exploring their own sense of connectedness to the world around them and their place in it. Most students take part in tefilah every day and a communal tefilah becomes central in the older grades.

The school believes that a connection to Israel is integral to establishing a strong Jewish identity. By the fifth grade, the school begins to introduce the history and culture of Israel through classroom discussion, reading material and projects.

Pluralism and egalitarianism are expressed in the way CESJDS approaches study and prayer with respect given to the traditions of each family's practice are respected.

Upper School students follows a nine-period curriculum (run on a block schedule with six periods per day). The Upper School's academic focus is based on Torah L'Shmah, teaching students to "become lifelong learners, inspired by a love of learning for the sake of learning". The school places a priority on critical, independent and creative thought and expression in the classroom.

A challenging academic program is paralleled by the teaching of an appreciation for the spiritual and ethical guidance offered by Judaism. The school remains committed to creating a caring, moral community based on the tenet of "V’ahavta L’rayakcha" where each individual is respected for his uniqueness.

Central to students' experience at CESJDS is "Kol Yisrael Arevim Zeh Ba Zeh", "all of Israel is responsible for one another and for the community". A commitment to community service is paramount with 80 recorded hours required for graduation.

Designed to prepare students for high achievement in college and in life, the dual-curriculum academic program for the High School is challenging. Students take from seven to nine academic courses within a rotating block schedule; a regular school day has six one-hour periods, and each class meets twice every three days. In order to ensure a solid foundation in both Judaic and General Studies, the school requires three Judaic and four General Studies core courses and two electives each year. Since all students take Hebrew, electives include Romance language courses as well as courses in the arts. The ninth course may be another core course, an elective, or a study hall.

Most departments offer three levels of High School courses: College Prep, Honors and Scholars. College Prep classes are rigorous and demanding, yet paced to promote the success of every student at the school. Honors classes offer students who are talented and interested in a particular discipline the opportunity to delve more deeply into the subject and to learn more sophisticated, discipline-oriented skills (e.g., literary criticism or mathematical reasoning). Scholars' classes offer gifted and dedicated students an intense academic experience. Although CESJDS does not offer AP courses because the school remains philosophically opposed to "teaching to a test", students do occasionally take AP tests.

The Upper School curriculum has formal classes ending in January for seniors and graduating in February, after which students can to go various school-sponsored trips. The first trip is a weeklong visit to Eastern Europe, including tours Poland and Prague, various concentration camps, and other former centers of Jewish life destroyed by the Holocaust. Students then have the option of continuing on a three-month tour of Israel, guided by the Alexander Muss High School in Israel. The majority of graduating seniors routinely choose to embark on both trips at an additional cost to the tuition.

Reflections – Gold Medalist rating from the Columbia Scholastic Press Association for its 2007, 2008, 2010, and 2011 editions, all the highest medalist rating CSPA offers; Superior rank in the 2005 and 2008 National Council of Teachers of English programs which recognize excellence in Student Literary Magazines, as well as Excellent rank in 2009 and 2011 programs (in 2005, out of 486 schools in the state of Maryland, Reflections was rated second in the entire State); First Place with Special Merit awards from the American Scholastic Press Association, the highest award ASPA offers, for the 2008, 2010, and 2011 editions.[4]

Collage – Gold Medalist ratings from the Columbia Scholastic Press Association, the highest medalist rating CSPA offers, in all years from 2004 through 2011, as well as a 2011 Gold Crown award; First Place with Special Merit from the American Scholastic Press Association, the highest medalist rating ASPA offers, 2006–10; First Class with Marks of Distinction from the National Scholastic Press Association with three marks in 2011[5] and one in 2012.

Melting Pot – First Place with Special Merit from the American Scholastic Press Association, the highest award ASPA offers, 2008-9, 2010–11,[6] and 2011-12.

Teams are usually divided into Varsity and Junior Varsity divisions. Many sports have boys' and girls' divisions. Almost all teams practice daily and compete with teams from other schools, primarily other schools within the Montgomery County private school community. The inaugural CESJDS hockey team won the MSHL Conference Championship in 2009, before losing in the state semi-finals. The team lasted from 2008/09-2010/11. For the 2013–14 season it was started back up again. No Lions teams have assigned practices or games on Friday. Only once has a team ever played a game on Friday, when a 2012 Varsity baseball game got postponed because of rain. To get the game done in time it started at 1:30 p.m., and the baseball team got out of class at 12:15 p.m.

In April 2006, three seniors who were participating in the school-sponsored program in Israel through the Alexander Muss High School were arrested by Israeli police for marijuana possession.[7] The marijuana was discovered by program guides, and the quantity was judged to be large enough to necessitate involving governmental authorities, according to Muss headmaster Chaim Fischgrund. Drug experts cited in a Jewish Standard article theorized that the students had intended to sell the marijuana.[8] These three students were expelled from the program; additionally, six other students were expelled on the basis of either having bought or used marijuana during program. Local police arrested two students on drug charges who were held overnight.[7]